Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/18—One oxygen or sulfur atom

Definitions

• the invention relates to new 1-arylpyrazoles, a process for their preparation and their use as agents for combating pests, in particular as insecticides and acaricides.
• pyrazole derivatives such as, for example, 1-cyclohexyl-5-[N,N-(dimethyl)-carbamoyloxy]-3-methylthiomethyl-pyrazole or 1-cyclohexyl-5-[N,N-(dimethyl)-carbamyloxy]-3-methylsulphonyl-methyl-pyrazole, have an insecticidal, nematicidal and fungicidal action.
• New 1-aryl-pyrazoles of the general formula (I) ##STR2## in which R 1 represents hydrogen, alkyl or halogenoalkyl,
• R 2 represents alkyl, halogenoalkyl or in each case optionally substituted aralkyl or aryl,
• R 3 represents hydrogen or halogen
• Ar represents optionally substituted phenyl or pyridyl
• n the number 0, 1 or 2
• R 2 represents alkyl, halogenoalkyl or in each case optionally substituted aralkyl or aryl,
• R 3 represents hydrogen or halogen
• Ar represents optionally substituted phenyl or pyridyl
• n the number 0, 1 or 2
• 1-arylpyrazoles of the general formula (I) according to the invention exhibit a considerably better insecticidal and acaricidal activity than the pyrazole derivatives known from the prior art, such as, for example, 1-cyclohexyl-5-[N,N-(dimethyl)-carbamyloxy]-3-methylthiomethyl-pyrazole or 1-cyclohexyl-5-[N,N-(dimethyl)-carbamyloxy]-3-methylsulphonylmethyl-pyrazole, which are closely related compounds chemically and from the point of view of their action.
• Formula (I) provides a general definition of the 1-aryl-pyrazoles according to the invention.
• Preferred compounds of the formula (I) are those
• R 1 represents hydrogen, or represents in each case straight-chain or branched alkyl or halogenoalkyl with 1 to 4 carbon atoms and, where appropriate, 1 to 9 identical or different halogen atoms,
• R 2 represents in each case straight-chain or branched alkyl or halogenoalkyl with in each case 1 to 8 carbon atoms and, where appropriate, 1 to 17 identical or different halogen atoms, or represents phenylalkyl or phenyl with, where appropriate, 1 to 4 carbon atoms in the straight-chain or branched alkyl part and in each case optionally monosubstituted or polysubstituted by identical or different substituents, possible substituents on the phenyl in each case being: halogen, cyano, nitro and in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl and halogenoalkylsulphonyl with in each case 1 to 4 carbon atoms in the individual alky
• R 3 represents hydrogen, fluorine, chlorine, bromine or iodine
• Ar represents phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, optionally monosubstituted or polysubstituted by identical or different substituents, possible substituents in each case being: cyano, nitro, halogen, in each case straight-chain or branched alkyl, alkoxy and alkoxycarbonyl with in each case 1 to 4 carbon atoms and in each case straight-chain or branched halogenoalkyl or halogenoalkoxy with in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, and a radical --S(O) m --R 4 , wherein R 4 represents amino, or represents in each case straight-chain or branched alkyl, alkylamino, dialkylamino or halogenoalkyl with in each case 1 to 4 carbon atoms in the individual alkyl parts and, in the case of the halogenoalkyl, with 1 to 9 identical or
• Particularly preferred 1-arylpyrazoles of the formula (I) are those
• R 1 represents hydrogen, methyl, ethyl, n- or i-propyl or trifluoromethyl
• R 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, chloromethyl, difluoromethyl, difluorochloromethyl, fluorodichloromethyl, trifluoromethyl, pentafluoroethyl, pentachloroethyl, fluorotetrachloroethyl, difluorotrichloroethyl, trifluorodichloroethyl, tetrafluorochloroethyl, heptafluoropropyl, chloroethyl, bromoethyl, chloropropyl or bromopropyl, or represents phenyl, benzyl or phenethyl, in each case optionally mono-, di- or tri-substituted by identical or different substituents, possible
• R 3 represents hydrogen, fluorine, chlorine or bromine
• Ar represents phenyl which is optionally mono-, di-, tri-, tetra- or pentasubstituted by identical or different substituents, or represents 2-pyridyl or 4-pyridyl, in each case optionally mono-, di-, tri- or tetrasubstituted by identical or different substituents, possible substituents on the phenyl or pyridyl in each case being: cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, difluoromethyl, pentafluoroethyl, tetra
• Formula (II) provides a general definition of the 5-amino-1-aryl-pyrazoles required as starting substances for carrying out the process according to the invention.
• R 1 , R 2 , Ar and n preferably represent those radicals which have already been mentioned as preferred for these substituents and indices in connection with the description of the substances of the formula (I) according to the invention.
• the 5-amino-1-aryl-pyrazoles of the formula (II) are the subject of commonly assigned application Ser. No. 690,347, filed Jan. 10, 1985, now pending and Ser. No. 858,475, filed Apr. 30, 1986, now pending, corresponding to German Patent Application Nos. P 3 402 308 and 3 517 843.
• R 2 has the abovementioned meaning
• Hal 1 represents halogen, in particular chlorine, bromine or iodine,
• a diluent such as, for example, methanol or ethanol
• a reducing agent such as, for example, sodium borohydride or sodium dithionite
• a base such as, for examle, sodium hydroxide or potassium carbonate
• R 2 has the abovementioned meaning
• Hal 2 represents halogen, in particular fluorine, chlorine, bromine or iodine,
• R represents hydrogen, or represents in each case optionally substituted alkanoyl or aroyl, and preferably represents hydrogen, or represents acetyl, or represents propionyl, or represents trifluoroacetyl, or represents optionally substituted benzoyl, such as, for example, 3-chlorobenzoyl or 4-nitrobenzyl, if appropriate in the presence of a diluent, such as, for example, methylene chloride, if appropriate in the presence of a catalyst, such as, for example, ammonium molybdate, and if appropriate in the presence of an acid-binding agent, such as, for example, sodium carbonate or sodium bicarbonate, at temperatures between 0° C. and 50° C.
• a diluent such as, for example, methylene chloride
• a catalyst such as, for example, ammonium molybdate
• an acid-binding agent such as, for example, sodium carbonate or sodium bicarbonate
• the 4-thiocyanato-5-aminopyrazoles of the formula (III) are known in some cases (compare, for example, Farmaco Ed. Sci. 38, 274-282 (1983). They are obtained, for example, by a process in which 4-unsubstituted 5-aminopyrazoles of the formula (VI) ##STR58## in which R 1 and Ar have the abovementioned meaning, are reacted with ammonium thiocyanate in the presence of bromine and acetic acid at temperatures between -20° C. and +20° C.
• the bis-(pyrazole) disulphides of the formula (IV) are not yet known. They are obtained by a process in which the 4-thiocyanato-5-amino-pyrazoles described above, of the formula (III), are reacted with aqueous hydrochloric acid, if appropriate in the presence of a diluent, such as, for example, ethanol, at temperatures between 20° C. and 120° C.
• a diluent such as, for example, ethanol
• the halides of the formula (V) are generally known compounds of organic chemistry.
• the 4-unsubstituted 5-aminopyrazoles of the formula (VI) are known in some cases (compare, for example, J. Org. Chem. 36, 2972-2974 (1971) or J. Hetero-cyclic Chemistry 7, 345-349 (1970); and C.A. 62: 13137c).
• R 5 represents hydrogen or alkoxycarbonyl
• A represents halogen, hydroxyl, alkoxy, amino or dialkylamino
• a diluent such as, for example, ethanol or glacial acetic acid
• a reaction auxiliary such as, for example, sodium acetate
• Ar, R 1 and R 5 have the abovementioned meaning, and these are cyclized in a 2nd stage, if appropriate in the presence of a diluent, such as, for example, ethylene glycol monoethyl ether, at temperatures between +50° C.
• arylhydrazines of the formula (IX) are known (compare, for example, U.S. Pat. No. 4,127,575; U.S. Pat. No. 3,609,158; DE-OS (German Published Specification) No. 2,558,399; and J. Chem. Soc. C, 1971, 167-174), or they can be prepared by processes which are known in principle, in a simple analogous manner (compare Houben-Weyl "Methoden der organischen Chemie" ("Methods of Organic Chemistry") Volume X, 2 page 203, Thieme Verlag Stuttgart 1967).
• the acrylonitrile derivatives of the formula (X) are generally known compounds of organic chemistry.
• the sulphenyl halides of the formula (VII) are generally known compounds of organic chemistry.
• the oxidizing agents of the formula (VIII) are likewise generally known compounds of organic chemistry.
• Possible diluents for carrying out the process according to the invention are all the solvents which are usually customary for such diazotization reactions.
• Solvents which are preferably used are hydrocarbon halides, such as chloroform or bromoform, or aqueous acids, such as, for example, hydrogen halide acids or sulphuric acid, the acid component simultaneously functioning as the reagent and/or as the reaction auxiliary. If bromoform is used as the diluent, as a rule the corresponding 5-bromo-pyrazoles are obtained, bromoform simultaneously functioning as the diluent and as the reagent.
• the process according to the invention is carried out in the presence of an inorganic or organic nitrite.
• nitrites are all the nitrite compounds usually customary for such diazotization reactions.
• Nitrites which are particularly preferably used are alkali metal nitrites, such as, for example, sodium nitrite, or alkyl nitrites, such as, for example, t-butyl nitrite.
• the process according to the invention is carried out in the presence of a hydrogen halide acid.
• a hydrogen halide acid 1-aryl-pyrazoles of the formula (I) in which the radical R 3 represents a halogen radical corresponding to the anion of the hydrogen halide acid used are obtained as reaction products.
• aqueous solutions of hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid are preferably used.
• reaction auxiliaries are, in particular, strong mineral acids, such as sulphuric acid or phosphoric acid, or the abovementioned hydrogen halide acids, which in this case simultaneously act as the reagent and as the catalyst.
• the process according to the invention can be carried out in the presence of a suitable reducing agent.
• a suitable reducing agent which is particularly preferably used in these cases is hypophosphorous acid (H 3 PO 2 ).
• reaction temperatures can be varied within a substantial range in carrying out the process according to the invention.
• the reaction is in general carried out at temperatures between -30° C. and +60° C., preferably at temperatures between -20° C. and +40° C.
• nitrite if appropriate 1.0 to 20.0 moles, preferably 1.0 to 10.0 moles, of hydrogen halide acid, if appropriate 1.0 to 50.0 moles, preferably 1.0 to 20.0 moles, of reducing agent and if appropriate 1.0 to 20.0 moles, preferably 1.0 to 10.0 moles, of mineral acid used as a reaction auxiliary are employed per mole of 5-amino-1-aryl-pyrazole of the formula (II).
• nitrite is usually added here in small portions, if appropriate dissolved in a suitable diluent, to the reaction mixture consisting of 5-amino-1-aryl-pyrazole of the formula (II), mineral acid, diluent and hydrogen halide acid or reducing agent.
• a suitable diluent consisting of 5-amino-1-aryl-pyrazole of the formula (II), mineral acid, diluent and hydrogen halide acid or reducing agent.
• reaction products of the formula (I) are worked up and isolated by customary methods, for example by filtering off crystalline products or by extraction with a suitable organic solvent. Identification is by the melting point or proton nuclear magnetic resonance spectrum.
• p represents the number 1 or 2
• R represents hydrogen, or represents in each case optionally substituted alkanoyl or aroyl, and in particular represents hydrogen, or represents acetyl, propionyl or trifluoroacetyl, or represents optionally substituted benzoyl, such as, for example, 3-chlorobenzoyl or 4-chlorobenzoyl, if appropriate in the presence of a diluent, such as, for example, methylene chloride, and if appropriate in the presence of a catalyst, such as, for example, ammonium molybdate, and if appropriate in the presence of an acid-binding agent, such as, for example, sodium carbonate or sodium bicarbonate, at temperatures between 0° and 50° C. (compare also the preparation examples).
• a diluent such as, for example, methylene chloride
• a catalyst such as, for example, ammonium molybdate
• an acid-binding agent such as, for example, sodium carbonate or sodium bicarbonate
• the active compounds are well tolerated by plants, have a favorable level of toxicity to warm-blooded animals, and are suitable for combating animal pests, especially insects, arachnida and nematodes, which are encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development.
• animal pests especially insects, arachnida and nematodes, which are encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development.
• the abovementioned pests include:
• Isopoda for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
• Diplopoda for example, Blaniulus guttulatus.
• Chilopoda for example, Geophilus carpophagus and Scutigera spec.
• Symphyla for example, Scutigerella immaculata.
• Thysanura for example, Lepisma saccharina.
• Collembola for example, Onychiurus armatus.
• Orthoptera for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, melanoplus differentialis and Schistocerca gregaria.
• Dermaptera for example, Forficula auricularia.
• Isoptera for example, Reticulitermes spp.
• Anoplura for example Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp.
• From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma Lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata Lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp.
• Psylla spp From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia Litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chils s
• Hymenoptera From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp, Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratiti
• Siphonaptera for example, Xenopsylla cheopis and Ceratophyllus spp.
• From the order of the Arachnida for example, Scorpio maurus and Latrodectus mactans.
• Acarina for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chlorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.
• the active compounds according to the invention have an action not only against plant pests, hygiene pests and pests of stored products, but also in the field of veterinary medicine against animal parasites (ectoparasites), such as scale ticks, leather ticks, hunting mites, chiggers, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas.
• animal parasites ectoparasites
• ectoparasites such as scale ticks, leather ticks, hunting mites, chiggers, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas.
• the active compounds according to the invention are distinguished by a powerful insecticidal and acaricidal activity. They can be used with particularly good success against insects which damage plants, such as, for example, against the larvae of the mustard beetle (Phaedon cochleariae) and against mites which damage plants, such as, for example, against the common spider mite (Tetranychus urticae). In addition, they are also outstandingly suitable for combating soil insects and can be used, for example, for combating Phorbia antiqua grubs.
• the active compounds according to the invention furthermore have a powerful action against hygiene pests and pests of stored products, and can be used, for example, for combating the house fly (Musca domestica), for combating the common corn weevil (Sitophilus granarius) or for combating the Madeira cockroach (Leucophaea maderae).
• the active compounds according to the invention can moreover be used with particularly good success for combating warmblooded pests which live as parasites, such as, for example, against the larvae of the gold fly (Lucilia cuprina) or against biting flies (Stomoxys calcitrans).
• the active compounds according to the invention also have a good fungicidal activity when applied in corresponding amounts, and can be used, for example, for combating Botrytis and Venturia species.
• the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and syntheteic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
• customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and syntheteic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
• formulations are produced in known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
• extenders that is, liquid solvents, liquefied gases under pressure, and/or solid carriers
• surface-active agents that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• liquid solvents there are suitable in the main: aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water; by liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers
• Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules and latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
• trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• the formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, baits, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• active compounds such as insecticides, baits, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• the insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms.
• the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents.
• Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
• the active compound content of the use forms prepared from the commercially available formulations can vary within wide limits.
• the active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
• the active compounds When used against hygiene pests and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
• the active compounds which can be used according to the invention are also suitable for combating insects, mites, ticks and the like in the field of livestock husbandry and animal breeding, it being possible to achieve better results, for example higher milk yields, a heavier weight, a more attractive animal coat, a longer life and the like, by combating the pests.
• the active compounds according to the invention are used in a known manner in this field, such as by oral administration, for example in the form of tablets, capsules, drinks and granules, by dermal application, for example in the form of dipping, spraying, pouring on and spotting on, and dusting, and by parenteral administration, for example in the form of an injection, and furthermore by the "feed-through” method.
• oral administration for example in the form of tablets, capsules, drinks and granules
• dermal application for example in the form of dipping, spraying, pouring on and spotting on, and dusting
• parenteral administration for example in the form of an injection
• Use in the form of shaped articles neck collar or ear tag
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of the active compound of the desired concentration and are infested with mustard beetle larvae (Phaedon cochleariae), as long as the leaves are still moist.
• the destruction in % is determined. 100% means that all the larvae have been killed; 0% means that none of the larvae has been killed.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Bean plants Phaseolus vulgaris which are heavily infested with the common spider mite or two-spotted spider mite (Tetranychus urticae) in all stages of development are treated by being dipped into the preparation of the active compound of the desired concentration.
• the destruction in % is determined. 100% means that all the spider mites have been killed; 0% means that none of the spider mites has been killed.
• Test insect Phorbia antiqua maggots (in the soil)
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
• the preparation of active compound is intimately mixed with soil.
• the soil is filled into pots and the pots are left to stand at room temperature.
• test insects After 24 hours, the test insects are introduced into the treated soil, and after a further 2 to 7 days the degree of effectiveness of the active compound is determined in % by counting the dead and live test insects. The degree of effectiveness is 100% if all the test insects have been killed and is 0% if just as many test insects are still alive as in the case of the untreated control.
• Test insects Musca domestica (resistant)
• the condition of the tests insects is checked continuously. The time required for a 100% knock-down effect is determined.
• the condition of the test insects is checked 3 days after the test has been set up.
• the destruction in % is determined. 100% means that all the test insects have been killed; 0% means that none of the test insects has been killed.
• Test insects Leucophaea maderae
• the condition of the test insects is checked 3 days after the test has been set up.
• the destruction in % is determined. 100% means that all the test insects have been killed; 0% means that none of the test insects has been killed.
• Emulsifier 35 parts by weight of ethylene glycol monomethyl ether; 35 parts by weight of nonylphenol polyglcol ether.
• the active substance in question is mixed with the stated solvent in a ratio of 1:2 and the concentrate thus obtained is diluted with water to the desired concentration.
• Test insects Blatella germanica
• the condition of the test insects is checked 3 days after the commencement of the experiments.
• the destruction in % is determined.
• the compounds of the following examples showed a destruction of 100% at a maximum concentration of 0.2%: 18, 22, 21, 23, 45, 25, 46, 48, 50, 55, 62, 65, 66, 71, 73, 12, 4, 74, 27, 79, 82, 83, 34, 30, 85, 88, 95, 97, 99, 101, 102, 80, 96.

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Citations (6)

• 1985
  • 1985-08-21 DE DE19853529829 patent/DE3529829A1/de not_active Withdrawn
• 1986
  • 1986-08-04 ZW ZW153/86A patent/ZW15386A1/xx unknown
  • 1986-08-04 US US06/893,133 patent/US4820725A/en not_active Expired - Fee Related
  • 1986-08-11 EP EP86111075A patent/EP0216102A1/de not_active Withdrawn
  • 1986-08-11 PT PT83184A patent/PT83184A/pt unknown
  • 1986-08-13 SU SU864027940A patent/SU1447265A3/ru active
  • 1986-08-14 JP JP61189736A patent/JPS6245577A/ja active Pending
  • 1986-08-14 AU AU61142/86A patent/AU6114286A/en not_active Abandoned
  • 1986-08-18 IL IL79756A patent/IL79756A0/xx unknown
  • 1986-08-18 OA OA58933A patent/OA08389A/xx unknown
  • 1986-08-19 DD DD86293733A patent/DD258164A5/de unknown
  • 1986-08-19 GR GR862156A patent/GR862156B/el unknown
  • 1986-08-19 FI FI863350A patent/FI863350A/fi not_active Application Discontinuation
  • 1986-08-19 MA MA20984A patent/MA20756A1/fr unknown
  • 1986-08-20 KR KR1019860006865A patent/KR870002080A/ko not_active Application Discontinuation
  • 1986-08-20 ZA ZA866277A patent/ZA866277B/xx unknown
  • 1986-08-20 BR BR8603971A patent/BR8603971A/pt unknown
  • 1986-08-20 DK DK397086A patent/DK397086A/da not_active Application Discontinuation
  • 1986-08-20 PL PL1986261086A patent/PL261086A1/xx unknown
  • 1986-08-20 ES ES8601223A patent/ES2001106A6/es not_active Expired
  • 1986-08-21 HU HU863641A patent/HUT45024A/hu unknown
  • 1986-08-21 CN CN198686105140A patent/CN86105140A/zh active Pending

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